3,3'-Neotrehalosadiamine

Base Information

• Chemical Name: 3,3'-Neotrehalosadiamine
• CAS No.: 104196-14-7
• Molecular Formula: C12H24 N2 O9
• Molecular Weight: 340.331
• DSSTox Substance ID: DTXSID80146339
• Nikkaji Number: J135.573B
• Wikidata: Q27145213
• Mol file: 104196-14-7.mol

Synonyms:3,3'-diamino-3,3'-dideoxy-alpha,beta-trehalose;3,3'-neotrehalosadiamine;BMY 28251;BMY-28251;BU 2797;BU-2797

Chemical Property of 3,3'-Neotrehalosadiamine

Chemical Property:

• Boiling Point: 711.4oC at 760 mmHg
• Flash Point: 384.1oC
• PSA: 201.11000
• Density: 1.65g/cm3
• LogP: -4.06380
• XLogP3: -4.7
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 340.14818035
• Heavy Atom Count: 23
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

3,3'-NEOTREHALOSADIAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)N)O)O)N)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)N)O)O

Technology Process of 3,3'-Neotrehalosadiamine

There total 6 articles about 3,3'-Neotrehalosadiamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-azido-3-deoxy-α-D-glucopyranosyl-(1→1')-3-azido-30-deoxy-b-D-glucopyranoside (1417719-77-7) → 3-amino-3-deoxy-a-D-glucopyranosyl-(1→1')-3'-amino-3'-deoxy-b-D-glucopyranoside (104196-14-7)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; water; for 48h; Inert atmosphere;

DOI:10.1016/j.tet.2012.10.058

Reference yield:

C33H38N6O9 → 3-amino-3-deoxy-a-D-glucopyranosyl-(1→1')-3'-amino-3'-deoxy-b-D-glucopyranoside (104196-14-7)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; water; at 20 ℃; under 760.051 Torr; Acidic conditions;

DOI:10.1002/cbic.201800656

Reference yield:

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0) → 3-amino-3-deoxy-a-D-glucopyranosyl-(1→1')-3'-amino-3'-deoxy-b-D-glucopyranoside (104196-14-7)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium acetate / N,N-dimethyl-formamide / 18 h

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -80 - -40 °C / Molecular sieve

3: sodium methylate / methanol / 4 h / 20 °C

4: palladium on activated charcoal; hydrogen / water; methanol / 48 h / Inert atmosphere

With ammonium acetate; trimethylsilyl trifluoromethanesulfonate; palladium on activated charcoal; hydrogen; sodium methylate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.10.058

upstream raw materials:

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

2,4,6-tri-O-acetyl-3-azido-3-deoxy-a-D-glucopyranosyl-(1→1')-2',4',6'-tri-O-acetyl-3'-azido-3'-deoxy-b-D-glucopyranoside

3-azido-3-deoxy-α-D-glucopyranosyl-(1→1')-3-azido-30-deoxy-b-D-glucopyranoside

Refernces

• 1、 Anjum, Shazia,Vetter, Natasha D.,Rubin, Joseph E.,Palmer, David R.J.. "Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks". . p. 816 - 825. Retrieved 2013/07/25.